I first went to chail way back in Sep 2004 with some biker friends. The good thing about chail is accessibility and the lack of commercialisation, plus the fact that it recieves snow every year too.One can reach Chail (from Delhi) by taking the NH1 to Ambala, and then heading towards chandigarh by taking NH22. Few kms before Chandigarh, take a right for Kalka. Kalka is where the hill climb starts and Chail is another 70-75kms more. Roads are in good shape and are wide too.
Lot of good dhabas/restaurants on the way. At solan, take a divertion to the right for the narrow (as compared to the kalka-solan one) road up to Chail. There are a few hotels in Chail along with Himachal tourism’s. Chail in itself is a small town and there isnt much to see. The highest cricket ground in the world is a worth seeing place, so is the chail palace. I would recommend you to carry on to Kurfi from there (snow/black ice on the road from dec to march, take precaution) and then make a loop by coming back via shimla-solan-kalka-delhi. The lack of tourists also mean Chail gets deserted after 9pm.
If you are a couple, dont head out alone. for families its ok, no issues. Lot of monkeys around and so keep the room windows closed. there are good expensive resorts on the Chail-Kufri road, worth a stay if you wish to be one with nature.PS : if travelling between late dec and mid feb, take precautions. it can snow heavily between chail-kufri-shimla and the roads have a lot of black ice.